DE611323C - Process for the preparation of photographic emulsions which are sensitive to long waves of the spectrum - Google Patents

Process for the preparation of photographic emulsions which are sensitive to long waves of the spectrum

Info

Publication number
DE611323C
DE611323C DEI41708D DEI0041708D DE611323C DE 611323 C DE611323 C DE 611323C DE I41708 D DEI41708 D DE I41708D DE I0041708 D DEI0041708 D DE I0041708D DE 611323 C DE611323 C DE 611323C
Authority
DE
Germany
Prior art keywords
sensitive
dye
spectrum
photographic
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DEI41708D
Other languages
German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Application granted granted Critical
Publication of DE611323C publication Critical patent/DE611323C/en
Expired legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • G03C1/14—Methine and polymethine dyes with an odd number of CH groups
    • G03C1/18—Methine and polymethine dyes with an odd number of CH groups with three CH groups

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Indole Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Description

Die Erfindung bezieht sich auf photographische, Kchtempfindlich machende Massen und photographische Präparate, wie Emulsionen oder Platten oder mit Emulsionen überzogene Filme. Es ist bekannt, daß eine normale photographische. Emulsion gegen Lichtstrahlen nur empfindlich, gemacht wird innerhalb der. Wellenlänge von etwa 360 bis 500 Millimikron und daß durch geeignete Behandlung, beispielsweise durch. Baden, !einer photographischen Platte in einer verdünnten Lösungeines lichtempfindlich, machenden Mittels die Emulsion gegen Licht anderer Wellenlängen empfindlich wird; aber es ist schwierig, die Empfindlichkeit nach Belieben in jeder gewünschten Weise zu vergrößern oder zu vermindern.The invention relates to photographic, sensitizing compositions and photographic preparations such as emulsions or plates or coated with emulsions Movies. It is known that a normal photographic. Emulsion against light rays only sensitive, is made within the. Wavelength from about 360 to 500 millimicrons and that by suitable treatment, for example by. Baden,! A photographic one Plate in a dilute solution of a photosensitizing agent the emulsion becomes sensitive to light of other wavelengths; but it's difficult the sensitivity to increase or decrease in any desired manner as desired.

Zweck der vorliegenden Erfindung ist, lichtempfindlich machende Massen zu schaffen, welche photographische Emulsionen gegen Lichtstrahlen in der roten Gegend des Spektrums empfindlich machen. Ein weiterer Zweck der Erfindung besteht darin, photographische Emulsionen zu schaffen, die gegen rote Lichtstrahlen empfindlich sind. Außerdem sollen Platten und Filme mit solchen lichtempfindlichen Emulsionen versehen werden. The purpose of the present invention is to provide photosensitive compositions, which photographic emulsions against light rays in the red region of the spectrum make sensitive. Another purpose of the invention is photographic To create emulsions that are sensitive to rays of red light. In addition, records and films with such light-sensitive emulsions are provided.

Diese Zwecke werden gemäß der Erfindung durch die Verwendung von unsymmetrischen Polymethinfarbstoffen folgender Zusammensetzung erzielt:These purposes are achieved according to the invention through the use of unbalanced Polymethine dyes of the following composition achieved:

i.Farbstoff von der Formeli.Dye of the formula

-CH = CH-CH =-CH = CH-CH =

C2H3 C 2 H 3

Dieser Farbstoff kann durch Kondensieren in Essigsäureanhydridlösung von 7 Gewichtsteilen 1:3:3- Trimethyl - 2 - methylenindolin und 16 Gewichtsteilen des Produktes, das durch Kondensation von Chinaldinäthj'odid mit Diphenylformamidin entsteht, erhalten werden. Die Menge des Essigsäureanhydrids soll 20 Gewichtsteile betragen, und die Lösung soll am Rückflußkühler 10 Minuten gekocht, alsdann etwas abgekühlt, mit 50 Gewichtsteilen heißem Wasser verdünnt und kräftig umgerührt werden. Es scheidet sich ein Farbstoff aus, der abfiltriert und gewaschen wird.This dye can be obtained by condensing in acetic anhydride solution of 7 parts by weight 1: 3: 3-trimethyl - 2 - methylene indoline and 16 parts by weight of the product that formed by condensation of quinaldinäthj'odid with diphenylformamidine, can be obtained. The amount of acetic anhydride should be 20 parts by weight, and the solution should be boiled on the reflux condenser for 10 minutes, then cooled slightly, diluted with 50 parts by weight of hot water and vigorously be stirred. A dye separates out, which is filtered off and washed will.

2. Farbstoff von der Formel2. Dye of the formula

C(CH3)2 C (CH 3 ) 2

Dieser Farbstoff kann durch Kochen am to Rückflußkühler einer Lösung in 160 Gewichtsteilen Essigsäureanhydrid, wozu 5 Gewichtsteile Natriumacetat hinzugefügt werden, von 18 Gewichtsteilen 2:3: 3-Trimethylindoleninmethjodid und 24 Gewichtsteilen des Produktes, welches man durch Kondensieren von 2-Methylbenzthiazoläthjodid mit Diphenylformamidin erhält, gewonnen werden. Nach ^stündigem Kochen wird das Gemisch mit 150 Gewichtsteilen heißem Wasser verdünnt und der ausgefällte Farbstoff durch Auslaugen mit Äther gereinigt.This dye can be obtained by refluxing a solution in 160 parts by weight Acetic anhydride, to which 5 parts by weight of sodium acetate are added, of 18 parts by weight of 2: 3: 3 trimethylindolenine methiodide and 24 parts by weight of the product obtained by condensing 2-methylbenzthiazolethiodide with diphenylformamidine receive, be won. After boiling for hours, the mixture becomes with Diluted 150 parts by weight of hot water and the precipitated dye by leaching purified with ether.

3. Farbstoff von der Formel3. Dye of the formula

CH,CH,

CH-CH' =CCH-CH '= C

C2H5 C 2 H 5

Dieser Farbstoff kann genau, wie bei 2 beschrieben, erhalten werden, nur daß man das CH3 This dye can be obtained exactly as described for 2, only that the CH 3

Produkt aus 2-Methylbenzoxazoläthjodid und Diphenylformamidin verwendet.Product made from 2-methylbenzoxazole ethiodide and diphenylformamidine used.

4. Farbstoff von der Formel4. Dye of the formula

Dieser Farbstoff wird analog erhalten aus 2-Methylbenzoxazoläthjodid und dem Produkt aus 2-Methylbenzthiazoläthjodid und Diphenylformamidin.This dye is obtained analogously from 2-methylbenzoxazole ethiodide and the product from 2-Methylbenzthiazoläthjodid and Diphenylformamidin.

Bei der Ausführung der Erfindung behandelt man eine photographische Emulsion mit unsymmetrischen Polymethinfarbstoffen, wie oben beschrieben, beispielsweise indem man eine, photographische Platte in einer verdünnten wässerigen Lösung des Färb Stoffs badet. Zweckmäßig wird <eine Lösung von 1 Teil Farbstoff in 2000 Teilen von 50 o/oigcm wässerigemIn practicing the invention, one treats a photographic emulsion with unsymmetrical polymethine dyes as described above, for example by a photographic plate is bathed in a dilute aqueous solution of the dye. A solution of 1 part dye is advisable in 2000 parts of 50 per cent. of water

Alkohol hergestellt. Diese Standardlösung wird für den Gebrauch mit etwa 20 Teilen Wasser verdünnt. 100 ecm der verdünnten Lösung werden für jede photographischePlatte voller Größe genommen und die Platte in die Lösiung eingetaucht, welche langsam umgerührt und mit der Platte etwa S Minuten in Berührung gehalten wird. Die Platte wird dann mit Wasser gewaschen und getrocknet.Alcohol made. This standard solution is made for use with approximately 20 parts of water diluted. 100 cc of the diluted solution becomes fuller for each photographic plate Taken size and immersed the plate in the solution, which was slowly stirred and is kept in contact with the plate for about 5 minutes. The plate is then with Water washed and dried.

So behandelte photögraphische Platten werden, wie in der nachstehenden Tabelle gezeigt, lichtempfindlich.Photographic plates treated in this way are photosensitive as shown in the table below.

Farbstoff (siehe vorstehende Formeln) auf die Platte angewandtDye (see formulas above) applied to the plate

=: CH-CH' ^=: CH-CH '^

■ N"■ N "

Platte wird lichtempfindlichPlate becomes sensitive to light

gegen Wellenlängeversus wavelength

(in Millimikron)(in millimicrons)

360 bis 653360 to 653

Farbstoff (siehe vorstehende Formeln) auf die Platte angewandtDye (see formulas above) applied to the plate

Platte wird lichtempfindlich g0 gegen Wellenlänge
(in Millimikron)Plate becomes light-sensitive g 0 against wavelength
(in millimicrons)

>C.> C.

bis 600up to 600

CH3^ CH3 CH 3 ^ CH 3

ΓΗΛΤ ■ ΓΗ Λ Τ ■

U2 U5 J t-.±l3 U 2 U 5 J t-. ± l 3

C6H4N ^>C—CH — CH — CH — C\ ^C6H4 360 bis 640C 6 H 4 N ^> C-CH-CH-CH-C \ ^ C 6 H 4 360 to 640

N- NN- N

C2H5 /X J C2H3 C 2 H 5 / X JC 2 H 3

Claims (2)

Patentansprüche:Patent claims: ι. Verfahren zur Herstellung von photographischen Emulsionen, die gegen lange Wellenlängen des Spektrums empfindlich sind, dadurch gekennzeichnet, daß der Emulsion unsymmetrische Polymethinfarbstoffe der Formelnι. Process for the preparation of photographic emulsions against long wavelengths of the spectrum are sensitive, characterized in that the emulsion is asymmetrical Polymethine dyes of the formulas CH = CH-CH =CH = CH-CH = ,C(CH3),
1N(CH3), C (CH 3 ),
1 N (CH 3 ) C2H5 C 2 H 5 C2HC 2 H Sx C(CH3),S x C (CH 3 ), CCH = CH-CH = C/CCH = CH-CH = C / N(CH3.N (CH 3 . CHo CH»CHo CH » ^C-CH = CH-CH =^ C-CH = CH-CH = C3 H5 ^^ JC 3 H 5 ^^ J CHq CH q /■/ ■ (i)(i) (2) 95(2) 95 (3)(3) ;C—CH = CH-CH = I; C-CH = CH-CH = I C2H5 C 2 H 5 (4)(4) zugesetzt werden.can be added. 2. Photographisches Material, dessen Emulsion nach dem Verfahren des 1. Anspruchs hergestellt ist.2. Photographic material, the emulsion of which by the method of claim 1 is made. BEBUN. GEDRUCKT IN DER REICHSDRUCKEREIBEBUN. PRINTED IN THE REICH PRINTING COMPANY
DEI41708D 1930-05-31 1931-05-31 Process for the preparation of photographic emulsions which are sensitive to long waves of the spectrum Expired DE611323C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB16911/30A GB354898A (en) 1930-05-31 1930-05-31 Improvements in and relating to the manufacture of photographic sensitisers

Publications (1)

Publication Number Publication Date
DE611323C true DE611323C (en) 1935-03-26

Family

ID=10085895

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI41708D Expired DE611323C (en) 1930-05-31 1931-05-31 Process for the preparation of photographic emulsions which are sensitive to long waves of the spectrum

Country Status (3)

Country Link
US (1) US2071898A (en)
DE (1) DE611323C (en)
GB (1) GB354898A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE750122C (en) * 1936-05-29 1944-12-14 Process for sensitizing multilayer photographic material for color photography
US2521705A (en) * 1946-08-21 1950-09-12 Du Pont Cyanine dyes
US3099630A (en) * 1955-11-15 1963-07-30 Monsanto Chemicals Water-soluble polymethine salts

Also Published As

Publication number Publication date
US2071898A (en) 1937-02-23
GB354898A (en) 1931-08-20

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